Hydrochloric Acid → HCID 11408052, compound

HRID 1785462Notes

Reaction equation

HRID 1785462 reaction equation
C([Si](C)(C)[O:6][CH:7]1[CH2:23][N:11]2[C:12](=[O:22])[CH:13]=[C:14]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[N:15]=[C:10]2[N:9]([C:24]2[CH:29]=[CH:28][N:27]=[C:26]([NH:30][CH:31]([C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)[CH3:32])[N:25]=2)[CH2:8]1)(C)(C)C.C(Cl)Cl.Cl.C([O-])(O)=O.[Na+]>CO>[OH:6][CH:7]1[CH2:23][N:11]2[C:12](=[O:22])[CH:13]=[C:14]([C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=3)[N:15]=[C:10]2[N:9]([C:24]2[CH:29]=[CH:28][N:27]=[C:26]([NH:30][CH:31]([C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)[CH3:32])[N:25]=2)[CH2:8]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6344DichloromethaneHCID 516892Sodium BicarbonateHCID 69068798HCID 69068798, compound

Product 1

HCID 11408052HCID 11408052, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 7-(tert-butyl-dimethyl-silanyloxy)-2-phenyl-9-[2-(1-phenyl-ethylamino)-pyrimidin-4-yl]-6,7,8,9-tetrahydro-pyrimido[1,2-a]pyrimidin-4-one (20 mg) in MeOH (3 mL)-DCM (1 mL) was treated with HCl (conc. 1.5 mL). After the mixture was stirred at room temperature for 16 h, it was neutralized with NaHCO3 (aq) and then extracted with DCM (3×). The organic layer was dried (Na2SO4) and concentrated to a solid that was purified on silica (1-3% 2N NH3—MeOH in DCM) to provide the product as a white solid. 1HNMR (400 MHz, DMSO-d6): 8.12 (d, J 5.6,1 H), 7.94 (m, 2H), 7.70 (m, 1H, NH), 7.44 (m, 3H), 7.32 (t, J 7.2, 2H), 19 (m, 1H), 708 (d, J 5.6,1H), 5.50 (ds, 1H, OH), 5.01 (m, 1H, ), 4.39 (b, 1H), 4.22 (bt, 1.5 H), 3.89 (d, J 4.8,1H), 3.68 (m, 0.5H), 3.3 (b, 1H), 1.45 (d, J 7.2, 3H). M+1: 441.

Workup

  1. extractionextracted with DCM (3×)
  2. dry with materialThe organic layer was dried (Na2SO4)
  3. concentrationconcentrated to a solid
  4. customthat was purified on silica (1-3% 2N NH3—MeOH in DCM)

Sources & evidence

ORD record
ord-aa3c7d36b47c4cf790899e0a97557549
Source dataset
uspto-grants-2009_03
Patent number
US07504403B2

Reaction notes

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